Catalysts for curable coating vehicle based upon aminoalkyloxy silanes and organic isocyanates

Abstract

Disclosed is a composition containing a novel ungelled resin in combination with an effective amount of a cure-promoting catalyst selected from the group consisting of triflic acid (i.e., trifluoromethane sulfonic acid), a neutralization product of triflic acid with ammonia, a neutralization product of triflic acid with an amine, a tetraalkyl ammonium salt of triflic acid, and mixtures of one or more of the aforesaid catalysts. The composition can be cured with moisture and/or with polyols and can be used to provide protective and/or decorative films on a variety of substrates. The novel ungelled resin comprises a compound corresponding to a specified formula (I) which compound typically is prepared by reaction of an aminoalkyloxy silane with an organic isocyanate. The ungelled resin contains a hydrolyzable group that is attached directly to silicon.

What is claimed is: 
     
       1. A composition comprising: (A) an ungelled resin containing a compound corresponding to the formula, ##STR16## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1,   R 1  independently represents H, a C 1  to C 10  alkyl radical, a C 1  -C 10  hydroxyalkyl radical or a radical corresponding to the formula ##STR17##  wherein Z represents H or C 1  to C 4  alkyl, and W represents ##STR18##  in which R 8  represents C 1  to C 8  alkyl, X represents a divalent radical containing at least 2 carbon atoms,   A represents a monovalent silicon-containing group corresponding to the formula ##STR19##  wherein R 2  independently represents hydrogen, a C 1  to C 10  alkyl group, a C 4  to C 10  cycloalkyl group, a C 6  to C 10  aryl group, or a monovalent aminoalkyl group, that is attached directly to Si,   Y represents a hydrolyzable group that is attached directly to Si   m is an integer ranging from 1 to 5,   e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and    wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and   (B) an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.   
     
     
       2. The composition of claim 1 wherein said hydrolyzable group Y is selected from the group consisting of ##STR20## and the C 2  to C 3  residue of a 1,2- or 1,3-glycol, wherein R 3  represents C 1  -C 7  alkyl, C 6  -C 8  cycloalkyl,   C 6  -C 8  aryl, or C 3  -C 8  alkoxyalkyl,   R 4  represents H or C 1  -C 4  alkyl,   R 5  and R 6  independently represent C 1  -C 4  alkyl, C 6  -C 8  cycloalkyl, or C 6  -C 8  aryl, and   R 7  represents C 4  -C 7  alkylene.   
     
     
       3. The composition of claim 2 wherein Q represents the residue from an isocyanate-functional polyisocyanate which is a reaction product of an organic polyisocyanate and a polyol having an average molecular weight ranging from 62 to about 3,000. 
     
     
       4. The composition of claim 3 wherein said polyol comprises a polyester polyol having an average molecular weight ranging from about 170 to about 2,000. 
     
     
       5. The composition of claim 1 additionally comprising an epoxy resin. 
     
     
       6. The composition of claim 5 wherein said epoxy resin contains an aliphatic diepoxide. 
     
     
       7. The composition of claim 3 wherein said polyol comprises a polyol containing at least one carboxylic acid group. 
     
     
       8. The composition of claim 5 wherein said cure-accelerating catalyst is a neutralization product of triflic acid with an amine. 
     
     
       9. The composition of claim 5 wherein said cure-accelerating catalyst is a tetraalkyl ammonium salt of triflic acid. 
     
     
       10. The composition of claim 5 wherein Q represents the residue from an isocyanate-functional polyisocyanate prepolymer which is a reaction product of an organic polyisocyanate and a polyol, which polyol has an average molecular weight ranging from 62 to about 3,000; R 1  represents hydrogen; A represents a monovalent silicon-containing group from an organosilicate and d equals zero. 
     
     
       11. The composition of claim 10 wherein said polyol comprises a polyol containing at least one carboxylic acid group. 
     
     
       12. A two-pack composition, a first pack comprising an ungelled resin containing a compound according to the formula, ##STR21## wherein Q represents the residue of an organic isocyanate having an average isocyanate functionality of at least 1, R 1  independently represents H or a C 1  to C 10  alkyl radical, a C 1  -C 10  hydroxyalkyl radical or a radical corresponding to the formula ##STR22##  wherein Z represents H or C 1  to C 4  alkyl, and W represents ##STR23##  in which R 8  represents C 1  to C 8  alkyl, X represents a divalent radical containing at least 2 carbon atoms,   A represents a monovalent silicon-containing group corresponding to the formula ##STR24##  wherein R 2  independently represents hydrogen, a C 1  to C 10  alkyl group, a C 4  to C 10  cycloalkyl group, a C 6  to C 10  aryl group, or a monovalent aminoalkyl group, that is attached directly to Si,   Y represents a hydrolyzable group that is attached directly to Si   m is an integer ranging from 1 to 5,   e is a positive integer wherein 1≦e≦11, d is zero or a positive integer wherein 0≦d≦10, and 3≦d+e≦11, and    wherein x is a positive number which is equal to or less than the average isocyanate functionality of said organic isocyanate; and a second pack comprising an effective amount of a cure-accelerating catalyst selected from the group consisting of trifluoromethane sulfonic acid, a neutralization product of trifluoromethane sulfonic acid with ammonia, a neutralization product of trifluoromethane sulfonic acid with an amine, a tetraalkyl ammonium salt of trifluoromethane sulfonic acid, and a mixture thereof.     
     
     
       13. The two pack composition of claim 12 additionally comprising an epoxy resin in said first pack. 
     
     
       14. The two pack composition of claim 13 wherein said epoxy resin contains an aliphatic diepoxide. 
     
     
       15. The two pack composition of claim 12 wherein said cure-accelerating catalyst is a neutralization product of triflic acid with an amine. 
     
     
       16. The two pack composition of claim 12 wherein said cure-accelerating catalyst is a tetraalkyl ammonium salt of triflic acid. 
     
     
       17. The two pack composition of claim 13 where for said resin, Q represents the residue from an isocyanate-functional polyisocyanate which is a reaction product of an organic polyisocyanate and a polyol, which polyol has an average molecular weight ranging from 62 to about 3,000; R 1  represents hydrogen; and A represents a monovalent silicon-containing group from an organosilicate and d equals zero. 
     
     
       18. The two pack composition of claim 17 wherein said polyol comprises a polyol containing at least one carboxylic acid group. 
     
     
       19. The composition of claim 1 wherein X represents a divalent radical containing at least 2 carbon atoms containing one or more groups selected from ether, amino, amido, carbamate, urea, and thio. 
     
     
       20. The two-pack composition of claim 12 wherein X represents a divalent radical containing at least 2 carbon atoms containing one or more groups selected from ether, amino, amido, carbamate, urea, and thio.